This invention relates to novel 3-halo-2-hydroxyalkyl carbamates, and a process for the preparation thereof.
The novel 3-halo-2-hydroxyalkyl carbamates of this invention are useful in preparing 2,3-epoxyalkyl carbamates which are useful as reactive diluents, ultraviolet light stable epoxy resins, additives to reduce the brittleness of epoxy resins, and as cross-linking agents in epoxy resins, polyurethanes and epoxy novolak systems.
Doss, U.S. Pat. No. 3,440,230, discloses a process for the preparation of a carbamate in which a polyisocyanate is reacted with an epoxy alcohol so as to form a carbamate in which the carbamate nitrogen has an active hydrogen atom attached thereto. The reaction to form the carbamate may be represented by the following equation: ##STR1## See also Kaufmann, U.S. Pat. No. 3,484,413 and Tesoro, U.S. Pat. No. 3,684,429. As described hereinbefore, the compounds made by this process result in a carbamate in which the carbamate nitrogen has an active hydrogen atom attached. Such compounds easily rearrange to prepare cyclic compounds, in particular, 4-hydroxymethyl-1,3-oxazolidin-2-ones. See U.S. Pat. No. 3,484,413 and Farrissey et al., J. of Heterocyclic Chem., 7, 331 (1970). This formation of cyclic compounds is undesirable as such rearrangements result under conditions at which the epoxy carbamates would normally be used.
What are needed are stable 3-halo-2-hydroxyalkyl carbamates.